Homes under $500K in Monticello, FL

26 for sale · 56 homes listed · Updated September 25, 2026 · Page 1 of 2

• 640 nautilus drive, Monticello 32344 $495,000 · 2 bd · 1 ba · 1,200 sqft
• 220 eaton street, Monticello 32344 $239,000 · 3 bd · 1 ba · 1,164 sqft
• 398 tecumseh road, Monticello 32344 $499,000 · 5 bd · 2 ba · 2,268 sqft
• 8156 waukeenah highway, Monticello 32344 $349,000 · 3 bd · 2 ba · 1,774 sqft
• 121 shumard court, Monticello 32344 $495,000 · 4 bd · 3 ba · 2,134 sqft
• 1628 north jefferson highway, Monticello 32344 $398,900 · 3 bd · 3 ba · 3,127 sqft
• 1164 oaklands plantation road, Monticello 32344 $259,900 · 3 bd · 2 ba · 1,456 sqft
• 670 poplar street, Monticello 32344 $149,900 · 3 bd · 1 ba · 1,312 sqft
• 870 shady lane, Monticello 32344 $150,000 · 3 bd · 1 ba · 1,366 sqft
• 1070 partridge lane, Monticello 32344 $298,900 · 3 bd · 2 ba · 1,351 sqft
• 1550 tennessee street, Monticello 32344 $200,000 · 3 bd · 2 ba · 1,304 sqft
• 285 mallard lane, Monticello 32344 $429,000 · 3 bd · 2 ba · 2,000 sqft
• 855 south waukeenah street, Monticello 32344 $424,900 · 4 bd · 3 ba · 1,798 sqft
• 947 piney woods road, Monticello 32344 $325,000 · 4 bd · 2 ba · 2,304 sqft
• 1150 sage street, Monticello 32344 $108,000 · 5 bd · 2 ba · 2,612 sqft
• 78 fen court, Monticello 32344 $470,000 · 3 bd · 2 ba · 1,806 sqft
• 112 long leaf drive, Monticello 32344 $250,000 · 3 bd · 2 ba · 1,980 sqft
• 490 north cherry court, Monticello 32344 $249,000 · 2 bd · 2 ba · 1,411 sqft
• 515 sunset drive, Monticello 32344 $299,900 · 3 bd · 2 ba · 2,583 sqft
• 1605 sweetbay court, Monticello 32344 $360,500 · 3 bd · 2 ba · 1,464 sqft
• 107 tarn way, Monticello 32344 $429,900 · 3 bd · 2 ba · 1,800 sqft
• 1420 tennessee avenue, Monticello 32344 $115,000 · 3 bd · 2 ba · 1,716 sqft
• 535 holly road, Monticello 32344 $357,000 · 3 bd · 2 ba · 1,326 sqft
• 360 bowman street, Monticello 32344 $254,900 · 3 bd · 2 ba · 1,235 sqft
• 30 pine needle trace, Monticello 32344 $249,000 · 3 bd · 2 ba · 1,210 sqft
• 1060 south water street, Monticello 32344 $175,000 · 2 bd · 1 ba · 1,488 sqft
• 34 west hummingbird lane, Monticello 32344 Active Under Contract $164,900 · 4 bd · 3 ba · 2,553 sqft
• 930 east pearl street, Monticello 32344 Active Under Contract $395,000 · 4 bd · 3 ba · 3,188 sqft
• 1511 spring hollow road, Monticello 32344 Active Under Contract $259,000 · 3 bd · 2 ba · 1,338 sqft
• 1012 south main avenue, Monticello 32344 Active Under Contract $379,000 · 3 bd · 2 ba · 2,280 sqft
• 254 woodland drive, Monticello 32344 Active Under Contract $450,000 · 3 bd · 2 ba · 2,239 sqft
• 120 larry south lane, Monticello 32344 Active Under Contract $227,900 · 3 bd · 2 ba · 1,323 sqft
• 339 silver lake road, Monticello 32344 Active Under Contract $375,000 · 3 bd · 3 ba · 2,706 sqft
• 51 tarn way, Monticello 32344 Active Under Contract $469,997 · 3 bd · 2 ba · 1,890 sqft
• 340 south waukeenah street, Monticello 32344 Active Under Contract $90,000 · 3 bd · 1 ba · 1,864 sqft
• 1680 willow road, Monticello 32344 Active Under Contract $435,000 · 3 bd · 2 ba · 1,919 sqft
• 520 east high street, Monticello 32344 Active Under Contract $175,000 · 3 bd · 2 ba · 1,825 sqft
• 2664 a west washington highway, Monticello 32344 Active Under Contract $325,000 · 5 bd · 2 ba · 2,659 sqft
• 73 west bryant court, Monticello 32344 Active Under Contract $295,000 · 4 bd · 2 ba · 1,760 sqft
• 12180 gamble road, Monticello 32344 Active Under Contract $299,900 · 3 bd · 2 ba · 1,575 sqft
• 196 private road, Monticello 32344 Active Under Contract $254,999 · 3 bd · 2 ba · 1,664 sqft
• 60 bob white trail, Monticello 32344 Active Under Contract $269,900 · 3 bd · 2 ba · 1,620 sqft
• 1565 sweetbay court, Monticello 32344 Active Under Contract $350,500 · 3 bd · 2 ba · 1,464 sqft
• 395 sunset drive, Monticello 32344 Active Under Contract $305,000 · 3 bd · 2 ba · 1,596 sqft
• 4081 gamble road, Monticello 32344 Active Under Contract $337,000 · 4 bd · 2 ba · 2,162 sqft
• 810 east dogwood street, Monticello 32344 Active Under Contract $235,000 · 3 bd · 1 ba · 1,700 sqft
• 304 limestone road, Monticello 32344 Active Under Contract $185,000 · 3 bd · 2 ba · 1,680 sqft
• 380 north jefferson street, Monticello 32344 Active Under Contract $279,000 · 3 bd · 2 ba · 1,957 sqft
• 195 coopers pond road, Monticello 32344 Active Under Contract $325,000 · 3 bd · 2 ba · 1,422 sqft
• 205 north rhodes street, Monticello 32344 Off market since Aug 2026 $345,000 · 3 bd · 2 ba · 2,766 sqft